


First Blush

by Anonymous



Category: Critical Role (Web Series)
Genre: F/M, Surprise feelings, blushy caleb, mischievous jester, the softest smut
Language: English
Status: Completed
Published: 2018-12-13
Updated: 2018-12-13
Packaged: 2019-09-17 05:39:24
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,260
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16968687
Author URL: https://archiveofourown.org/
Summary: From the kinkmeme prompt: "Twice now, Liam made a point to say that Jester's antics have made Caleb turn beet red. I want Jester noticing this and going out of her way to tease and fluster him, and eventually finding out how far down the red goes."





	First Blush

**Author's Note:**

> I filled my own prompt because YOLO

The best thing about having a bunch of multicolored friends, Jester decided, was that all of them made the prettiest picture just by walking around together. Fjord and Nott covered the lovely spectrum of green. Jester was blue, and Molly was purple. Beau and Caleb were their contrasty, earthy human colors. Later on, Caduceus brought his fun, funky color palette. And Yasha had that cool, monochromatic thing going on.  
  
It was just a shame that they were missing some warmer, redder hues. For one thing, it would remind her of her Momma, who she missed every day. For another, red was like, one of the most basic colors. How did one make a great painting without red, huh?  
  
Although, she'd noticed that sometimes Caleb could fill in the reds in the right circumstances.  
  
"There's a lot of people that inspect their _special packages._ You get to know yourself _real good_ , Caleb."  
  
When she said that, his face instantly flamed as red as his hair, though he otherwise kept his composure while they set up their date with the dodecahedron. As she left to tag along on Molly and Beau's adventures with mysterious substances, it occurred to Jester that teasing the wizard could turn out to be a _very_ entertaining new game.  
  
It was funny sometimes, the things that made Caleb blush. She'd expected a well placed naughty joke would continue to do the trick, but to her surprise, he often seemed unfazed. Sometimes _he'd_ even be the one with a wry joke. (Yup, she'd definitely heard him trying to get Kiri to repeat "edubation.")  
  
No, instead it was at times like when he almost shyly mentioned his ambitions to make a nice shelter for the group. "You're an enjoyable lot," he'd said softly, and his cheeks pinkened just a little. He'd endured the thanks and praise, shrinking into himself until the conversation moved on.  
  
Being the center of attention seemed to be the common thread, like when they all woke to the sight of Yasha with her blade at his throat. The brief panic was quickly replaced by excitement at the wizard's new look.   
  
"You have a little thing, you have a little dimple on your chin!" Jester exclaimed. "That's the cutest!" It really was! And as she watched, the dimple and the rest of his face bloomed red. With his cheeks newly bared, it was even easier to see the flush creeping all the way down his neck and disappearing into his scarf. Jester spared a moment to wonder how far the red would go, but it was rude probably to think about that when poor Caleb looked like he wanted to shrivel up and die, and right after he and Beau'd had a big fight so maybe she'd have to ask some other time.  
  
In Hupperdook, Jester got to learn that really pale humans apparently turned red when they got super extra drunk. Caleb had danced with her, clumsy in his drunkenness, but with deliberate steps that were probably more graceful when he was sober. That close, she could see that the tips of his ears, usually hidden in his scruffy hair, were also red. Although...could they be called tips? Humans and their round little ears! Caleb seemed so stiff and angular usually, but this part of him was soft. That was cute too.  
  
And then he called her Astrid, and the mood turned sad. Jester ended up tucking Caleb in bed as he sang silly little songs and she wished she could make him feel better.  
  
After...everything that happened in Shady Creek Run, Jester made it her mission in life to make her friends happy. In the name of keeping their spirits up, she spent the long trip south to her hometown flirting extra hard with Fjord, having cleric time with Caduceus, and having lots of girls' nights with Beau and Nott. (Girls' nights with everyone in the group included because there wasn’t really any private space in Caleb’s magic bubble, but it was the thought that counted.)  
  
Speaking of Caleb, he had gotten good at gently rebuffing her invitations to play travel games or chat, spending most of his time in the cart with his nose in a book.   
  
Frumpkin, however, had gotten very demanding of Jester's time. He kept coming to her for cuddles, sitting with her during watch, and weirdly, came looking for her when she went into the woods to take care of private _ladybusiness._ After three or four times of that, she scooped the cat up and took him back to his wizard and held him out saying, "Hey, Caleb, are you using Frumpkin to watch me pee?" Not that she'd be mad if he was, but she'd have liked to know about it beforehand.  
  
Caleb dropped his spellbook, and his face went white then flaming red in very quick succession. His mouth gaped comically and his hands flailed in a panic and he squeaked a bit before he was able to get out a strangled, "Nein, nein, Jester, no--!"  
  
And it was a punch in the gut to get such a vivid reaction from him. She suddenly realized that it had been weeks since she’d seen anything but grim determination on his face, and she was so flooded with unexpected relief that her head felt hazy and light, and she missed half of his stammering explanation.  
  
"...alone, after what happened last time! It’s only a precaution, not a, not a..."  
  
Jester decided to put him out of his misery and gave him a quick hug and a kiss on the cheek. "I get it Caleb, you don’t have to explain anymore. Thank you for worrying about me." And because she was still feeling giddy and his little ear was right in front of her, she whispered, "And I don’t kinkshame." That set off another round of sputters, and Jester giggled in delight as she felt for the first time in a long time that they would be okay.  
  
After that, the game was on again. Little teasing comments, some innuendo because it was fun and it usually got some interesting reaction out of him - a small smile, wry chuckle, or eyeroll at her very worst puns. Still, it wasn't the top prize, that pink flush. No, for that, Jester had to subtly escalate.   
  
She sketched him often, since he tended to blush and turn shy once he noticed he was being studied so closely. If Frumpkin was scarfing over Caleb's neck, Jester would be sure to give the cat some head scritches, and maybe, just _accidentally_ end up brushing her fingertips over some human ears as well. The first time, Caleb actually jumped, startled and maybe ticklish, too. Jester gave him a shrug and her best, "oops, what can you do?" smile.  
  
Jester kept at it, leaning in close over his shoulder when he was reading and making sure to be the first to grab his hands when he was in Frumpkin's eyes. She crowded in close when they settled in for long drinking sessions, her with her milk and him and the others with their ale. Caleb did generally turn rosy with enough drink, but when she wanted to speed things along, she curled her tail around his ankle and tickled up and down his calf.  
  
It was another funny thing about Caleb, that given how reluctant he was about things like eye contact, he didn't seem too bothered by these invasions of his personal space. Sure, he wasn't a touchy person--he didn't initiate contact--but he didn't flinch away or push Jester off him like she honestly expected the first time she mock swooned into his arms while playacting a scene from Tusk Love. He tolerated her soft touches and blatant cuddles even as they made him burn pink.  
  
As they got further and further out of the Empire, his general air of tension seemed to bleed out of him even more. His small smiles came just a bit easier, and his shoulders hunched a little less. Clearly, her concentrated contact campaign was doing him some good, so Jester took advantage of every chance to be close to him, for his sake, you know?   
  
By the time they made it to Nicodranas and the Lavish Chateau, everyone was road weary and looking forward to some rest and relaxation in real beds. Jester had just left her Momma and was making her way around to say goodnight to the others when she ran into Caleb in the hall.  
  
Oh no. She hadn't noticed in the dim light of the Chateau's lounge area or in her mother's dressing room, but here and now, she could see he was almost as red as the Ruby. She knew she hadn't just been around to make his face do that, and she was struck with a sudden and fierce worry.   
  
"Calebbb!" She palmed his face with both hands, only remembering at the last second to be gentle. And yep, he was warm, warmer than humans were supposed to be.  
  
"Caleb, are you sick? Are you hurt? You have to tell me so I can fix it, I'm the cleric, Caleb!"  
  
"No, no, I am alright, Jester. I'm just a bit sunburned from our beach trip." He removed her hands with a wince. "You know, we didn't see weather like that in the Empire."  
  
"I'm so sorry, Caleb, I should have thought of that! Next time, I can cast Protection from Energy on you. I won't let you burn!"  
  
He made an awkward, strangled sound and didn't meet her eyes, but that was nothing new.  
  
"Wait right here, my mom has some cream for sunburns."  
  
Jester doubled back to her mother's rooms then returned with the jar of ointment. Presenting it to him, she saw another golden opportunity and couldn't resist a lascivious smirk.  
  
"Cayyyy-leb. Do you want some help rubbing this into your _hard to reach_ places?"  
  
His face flared impossibly redder and he snatched the jar from her hand and mumbled something like "ThankyouImeannothankyougutennacht," and practically ran to the safety of his and Nott's room.  
  
When she got back to her own room, Beau asked what had her looking so pleased with herself. Jester laughed and said it was a secret, so Beau whacked her with a pillow, and then Jester was having her first pillow fight at her first sleepover in her childhood bedroom with one of her first (non-deity) friends. It was a pretty great night.  
  
Of course, good things never lasted long, and they were leaving (fleeing) Nicodranas sooner than she'd wanted. In a stolen ship. Were they pirates now?  
  
They'd just fought off a flock of harpies, and Jester was inspecting the damage to the sails when there was another commotion from the deck below her. Caleb had collapsed! Nott was crying out about his condition and begging for someone to administer mouth-to-mouth.  
  
Caleb's act was pretty scarily convincing, but Nott was a _lousy_ liar. Jester figured that this must be like Modern Literature, where Caleb played dead that one time during a fight (which, by the way, _so rude!_ They didn't tell anyone what they were doing and Jester got really worried for real!)  
  
Well. Three could play at that game, so Jester hopped down from her perch in the rigging, cradled Caleb's head in her hands, planted her lips on his, and blew into his mouth as hard as she could.  
  
Caleb "came to" coughing and sputtering, "That's not what I was expecting..."  
  
Jester beamed and said, "Oh good, you're alive." Whether from the scene they were making, or her over-exuberant lifesaving efforts, Caleb's face was the best shade of red she'd seen yet. She'd definitely have to draw this one later.  
  
Fjord wondered aloud how to prevent more such episodes and Nott insisted, "More friendship. Just more friendship."  
  
Yeah, okay. Jester could get behind that.

 

***

 

It was Caleb's ears that were her undoing. Months had gone by and they were unwinding in yet another tavern, after yet another day of chaotic fights and running away from the results of accidents and bad decisions. Molly and Caduceus were debating the finer points of various hallucinogenic plants. Beau was listening to Fjord critique her sailing knots and trying to look like she wasn't listening in on the other conversation. Nott was deep in her cups, with Yasha's enormous hand keeping her upright.  
  
Jester had plopped herself in Caleb's lap, which was a pretty new allowance. (She'd successfully argued that it's no fair that only Frumpkin gets to sit in his lap all the time, and tieflings are practically half cats anyway what with their pointy ears and tails. Caleb may have been _super_ drunk during that debate.) He still blushes and stammers when she does it, but otherwise doesn't argue.   
  
Jester had one arm slung around his shoulders for balance, and the shell of his left ear was perfectly in view, and it was pink. It was pink and little and round, and she actually drank half a tankard of ale this time, and combined with its cuteness and the post-battle high, she couldn't stop herself from taking a little nibble. Caleb immediately froze, going stock still. And that wasn't the only part of him that stiffened.  
  
Well now! Even though Jester thinks about dicks a lot, Caleb's hasn't crossed her mind too much. She'd seen it briefly way back in the bathhouse (admittedly, she'd been more distracted by Molly's decorations and Fjord's _all-of-that_ ). Caleb was soft and pale all over, right? She'd bet the rest of him could go just as red as his face. And it was suddenly of vital importance that she check. Just to make sure.  
  
So just as she'd come around to the idea that this was a _very_ welcome turn of events, Caleb leapt out of his seat, dumping her on the floor, and hightailed it to his room. But not before she caught the pained look on his face and suddenly her game wasn't just a game anymore. Not if it was making him feel like that.  
  
"Caleb wait!" She got up and hurried after him, ignoring the looks from her friends.  
  
Caleb was walking quickly, but Jester, panicked into a full on sprint, caught up to him easily in the hall outside their rooms. Without thinking, she crashed into his back and wrapped her arms around him.  
  
" _Cayleeebbb!_ I'm sorry, please don't be mad at me, I don't want you to be upset! You're one of my _very_ best friends and I like you so much, and I like teasing you, but if it's not good and you really really hate it I'll stop, I promise!"  
  
Caleb wasn't saying anything or moving in her hold. She reluctantly released him, hoping he wouldn't immediately run away again. There was still a nervous tension in him, but he seemed to be listening. That was good, right?  
  
"Caleb," she started again, willing him to hear her sincerity. "I'll go away if you want me to. I'll stop all the touching and comments and getting in your way. I'm sorry, and you are very important to me." And then, because she saw no good reason not to be forthright in matters of physical intimacy, "Also, I don't want you to be embarrassed because you got hard. It's really okay, because I thought about it, and I really want to make you come."  
  
That sent a jolt through him, and he huffed a startled laugh, shaking his head a bit. But when he finally turned to look at her, his tiny smile was a little exasperated and a lot fond.  
  
"If that's what you want...Can I at least kiss you first?"  
  
She threw her arms around him in a tight hug born of pure relief, then pulled back to give him that kiss. Caleb eased into it slowly, kissed her sweetly, and Jester's not ashamed to admit it - she swooned a teeny bit. This one definitely counted.  
  
Caleb's face was beautifully pink when they separated, and Jester suddenly remembered her musings on that front. "Can I do it now?"  
  
"Um, ja, that would be, ehm. Yes." He seemed unsure what to do next, but no matter. Jester had no problem with taking point on this.  
  
"Hold on tight, Caleb."  
  
"What? _Ack-!_ "  
  
Jester had ducked down, wrapped her arms around his thighs, and hauled him up and over her shoulder. She marched him to her room and dumped him on the bed, where he didn't quite bounce, the mattress was too shitty for that.   
  
"Was that okay?" she said with a smirk. She didn't really need to ask. His breathing had sped up, his eyes had gone wide, and while she carried him, she had definitely felt Little Caleb sit up and take notice.  
  
" _Yes,_ " he breathed.  
  
"That's good, Caleb." She crawled over him. "I'm going to make you feel _really good._ "  
  
Jester wrestled his bulky coat off (and was pleased to discover most of the lingering smell he carried around was from the Weird Wizard Things in the pockets and Caleb himself didn't smell that stinky anymore at all) and had started on his strappy thing when Caleb gently batted her hands away and removed his books with much more care than she would have bothered with. She sat back and used the time to strip out of her outer layers, down to her silky underthings. This distracted Caleb from his own undressing, and his hands hovered between them, hesitating. Jester took his hands and placed them over her shift. "Here, you can feel."   
  
He ran his fingertips over and over her back and sides, seeming entranced with the silky smooth fabric. Yes, he liked that _very much._  
  
While he did that, Jester worked on getting his shirt open, and just like she thought, he was flushed there too, and dotted with cute speckly freckles. Jester experimented, pressing her fingertips firmly into his skin, watching the flesh turn white before the blood rushed back to the surface. She drew long lines over his skin, painting fleeting patterns and swirls. On a whim, she sketched a line with one nail, not hard enough to break skin, but with a lot more bite than her fingers. The mark it left was a deeper red, and it lingered. Caleb let out a long, low groan. He was shaking under her.  
  
"Caleb? Are you okay?"  
  
"Ja..." He fought to keep still, with limited success. "It's been... a very long time for me."  
  
"Then I better not make you wait!" And she scooted down out of Caleb's reach and moved to attack his pants.  
  
Jester's seen a lot of dicks, okay, she never lied about that. But she _kinda sorta maybe_ fibbed in the sense that she let her friends believe that she also had a bunch of experience handling them as well. Which she didn't, but that was okay, because she had a pretty good idea what to do with them from intense (hands off) study.  
  
She got the rest of Caleb's clothes off, sat back on his thighs, and settled in just to take a good long look at first. Red, so very red like she'd thought, and already leaking a little. She paused in her scrutiny when she heard a whimper. Caleb's hands were clenched tight in the sheets at his sides, and he was gazing at her with pleading eyes.   
  
She grasped him gingerly and was utterly unprepared for the warmth. He was heat, and softness, and hardness all at once, and completely unlike any of the dozens of assorted sculpture dicks she'd painted up and played with one lazy afternoon. He reacted to every shift of her hand, panting and writhing a little, careful not to buck up and out of her grip.   
  
She moved her hand over him, watching his reactions, and it was fascinating. With one hand, she had someone completely at her mercy, and she felt powerful. But also... inexplicably lonely. When she'd observed the Ruby at work, her Momma was cool, and classy, and always in control. Did she also feel like something was missing?  
  
Jester's confidence was starting to falter just a bit at this realization, and then Caleb was stretching one hand out, trying to reach her. "Bitte...come back?"  
  
Jester could do that. She maneuvered back up to him, a little awkwardly, letting go of him at one point so she could find a good position. She ended up cuddled up close to his side, his lips and ears in easy kissing distance. His arms went back around her, and one hand came up to gently pet her hair. She could see right into his blue eyes in his red face. Blue like a blueberry, and he'd called her that once, and the memory rose up warm in her chest and spread outward and she needed to share that heat with him or else she'd burn up alone. She curled even closer to him, arms, legs, and tail wrapping him in a full body hug. She kissed him again, and felt quite a bit better for it.   
  
Honestly! Jester had started this endeavor with a goal in mind, and now she was getting distracted by this...sudden, floaty, romantic feeling for her friend who was mysterious and weird and funny and so, so sweet to her. She'd promised to make him feel good, and definitely wanted to follow through, so she wiggled a hand between them and took hold of Caleb's dick once more, struggling to stay on task when he began groaning and murmuring soft, probably Zemnian things into her neck.   
  
They continued moving together until he finally came with a gasp, his head tossed back and mouth open, face suffusing with yet another lovely shade of red that Jester was sure was entirely new. She was going to have to start cataloging them at this rate. No reason not to start now.  
  
Jester ended up sprawled directly on top of Caleb, and she rested her chin on her hands on his chest, looking up. (After she wiped them off. That was another thing that was as expected and yet also _not_.) Frumpkin sometimes perched on his belly or chest like this and she could now agree, it was a very good spot to be. Caleb was warm, and it put her close enough to admire the lingering flush on his face.   
  
Caleb’s hands had returned to the silk at her waist, moving in long, slow strokes as his breathing evened out. His fingers traced patterns over the fabric, then, seeming emboldened, dipped to the hem for just a moment.   
  
"Jester, is there...would you like me to do something for you?"  
  
"Hmm." She wanted to keep looking. "Maybe later. But thank you, Caleb!" She dropped a quick kiss to his chest. Then she poked the skin again, watching the colors shift in her fingers' wake. It was true, she did want to keep looking. But also, she felt the need to pause and take stock, of not only her first successful go at pleasing a sex partner, but also the feelings that had unexpectedly welled up in her in the moment.   
  
While she wondered where to start puzzling things out, Caleb's hands were warm on her waist, just holding. She liked that. But his brow had developed that little furrow he got when he was thinking too hard about something. She liked that less.  
  
"What's wrong Caleb?"   
  
"Nothing," he tried to assure. "I just can't believe... I suppose I don’t understand why you wanted to do this with me. And not someone more..." Caleb waved one hand in the air, seeming unable to find the words.  
  
It was a fair question and it deserved some thought, especially since from a different angle, Jester was already wondering the same thing. She propped her chin in one hand to think about it. What was nice about Caleb? He isn't smutty-novel-cover suuuper handsome like Fjord. Now that she's seen his dick up close, she's decided that it isn't as nice as Molly's (but still pretty good). But he is super responsive to the littlest teasing, flustering and turning red so easily which is really really cute.   
  
Caleb can get standoffish like the cats he likes so much when he's really absorbed in his books or new magic. It can be hard to get him to hang out and have fun with the group. He tries to pretend he doesn't care about their friends as much as he does, but then he makes her promise not to go walking off at night alone, and asks if her Momma loved her and took good care of her as a little girl. He laughs at her jokes. He hardly ever smiles or laughs for anyone else, but he laughs for her. She thought of the softness in his voice as he promised he would see her back home.  
  
There were lots of reasons, really. Too many to talk about all at once right now, but she could let him have at least one. So she smiled and snuggled into him, poking a nipple. "Cayyyy-leb. Pink is my favorite color."  
  
Maybe it was a little mean to deflect from the more serious thoughts she was having, but Caleb huffed out a little laugh. Jester _loved_ making him laugh, because he always seemed a little surprised that he _could_ laugh. So as long as it made him happy, Jester decided that it was a good answer. At least for now.  


**Author's Note:**

> Coda: _"Hey Beau, it's Jester. Caleb's naked in our room and I'll probably be naked in a bit too, so you maybe don't want to come-"_
> 
> _"-back to the room for awhile okay? I mean, I don't care, but Caleb says you have a rule not to talk about each other's-"_
> 
> _"-sex lives or something? You should probably stay with Nott tonight. Ohhh, or maybe see if Yasha wants some company if you know what I-"_
> 
> "...What the fuck, Jester."


End file.
